May 2025 — Adapting Fast, Living Fully
Clarity, Chaos, and What Comes Next
This month, I’m connecting a few big threads: generational shifts, AI disruption, personal optimization, and the growing urgency to reconnect with what’s real.
We’re just four Fridays from Memorial Day Weekend. Let that settle for a second.
One-third of 2025 is already behind us, and the pace of life only seems to pick up. I’ve been spending time lately exploring health, longevity, and the deeper patterns shaping how we live and work. And one thing is clear: we’re in a moment of real transition.
If we can recognize the shifts—generational, technological, physical—we can move with more clarity, lead with more intent, and build lives that actually feel good to live.
The Fourth Turning & an AI Future
If it feels like the ground is shifting beneath your feet, you're not imagining it.
We’re in a rare moment—a generational inflection point that Strauss and Howe called “The Fourth Turning.” These periods show up every 80–100 years and mark the collapse of old systems and the start of something new. Historically, they're turbulent. They're also necessary.
At the same time, AI has entered the chat. And it’s not quietly waiting in the wings—it’s reshaping how we work, make decisions, communicate, and create. It's moving faster than our systems, our policies, and in some cases, our ability to process what’s even happening.
That kind of pressure—generational, technological, cultural—forces adaptation. Some of us are rethinking how we lead. Others are reengineering how we live. Personally, I’ve found myself more focused on health, attention, time with family, and what actually matters.
This isn’t a season for coasting. It’s a time to pay attention, move with purpose, and decide who you’re becoming while the world reshapes itself around you.
P.S. Big thanks to Jesse for leading me down this rabbit hole—right when I had just started sleeping peacefully again. 😉
Operationalizing AI in Business
One pattern I keep seeing—at Atlassian’s Team25, at Planview Connect, and in the lead-up to ServiceNow Knowledge25—is the emergence of enterprise AI not as an add-on, but as a core capability for strategy and execution.
This isn’t hype. It’s happening. AI is being built directly into the planning stack—identifying priorities, mapping dependencies, surfacing risks, and even proposing staffing plans based on intent and available capacity. In many cases, the first draft of a roadmap or strategy isn't coming from a whiteboard session, it's coming from an LLM trained on your enterprise data.
We’re watching work planning evolve into something far more dynamic and adaptive. Decisions that once required a week of meetings and multiple decks are starting to happen in real time, with humans stepping in to guide, refine, and lead, not just gather inputs.
If you're in the business of building alignment, setting direction, or delivering value across silos—this shift matters. It changes how we lead. It changes how we scale. And it creates an opening for those who are willing to architect not just products, but new ways of working.
Get Ready for Whats Next:
Here are a few tools worth exploring to understand how enterprise AI is reshaping strategic planning and execution:
Atlassian Rovo – A new AI-powered work graph that connects people, work, and knowledge across Atlassian’s platform.
Planview Copilot – Embedded AI that surfaces portfolio insights and recommends actions across programs and value streams.
ServiceNow Now Assist – AI capabilities that accelerate decision-making across ITSM, HR, and strategic portfolio management.
ClickUp Brain / Notion AI – For smaller teams, these platforms are bringing intelligent summarization and task planning to the everyday workflow.
Coda + AI & GPT integrations – A modular doc-based platform for teams looking to prototype lightweight AI planning flows.
Pick one. Connect it to a real initiative. See what it gets right and where it needs you. Don’t wait for the “AI strategy” team to figure it out. This is your edge.
Be Easy to Find, Hard to Reach
One shift I’ve been leaning into this year is being easier to find, but harder to reach.
Not in a cold or inaccessible way; but in a focused, deliberate way. I’m treating my calendar and inbox like high-value real estate. Not everything gets a piece of it. Not everything should.
AI has helped here more than I expected. It drafts content, organizes thoughts, preps conversations, and takes the first pass at things that used to clutter my day. That space? I use it for what actually matters: leading, thinking, being present with my family, or having deeper conversations with the people who are in my circle for a reason.
My goal isn’t to disappear, but to design a life that’s built for what’s next. If this really is a generational turning, and the systems we’ve relied on are starting to give way, then clarity, boundaries, and intentional use of time aren’t luxuries. They’re survival skills.
Quick Tip: Try a Weekly Reset
Once a week, take 30 minutes to look ahead and ask:
What can only you do
What can be handed off to someone else
What can AI draft, prep, or automate
Start small. Let ChatGPT write a rough outline for your next team update. Use it to prep for a difficult conversation or summarize a meeting you missed.
You’re not outsourcing judgment. You’re protecting it.
And the space you create? That’s where your best work—and life—lives.
The Need for Adventure
The more time I spend thinking about where we’re headed, the more I find myself reflecting on where I’ve been—and where I came from.
I miss adventure. Honestly, I crave it.
Back when I was producing Orion’s Kin or growing up in Pennsylvania, getting off the grid wasn’t something I had to schedule. Off the grid was life. Every day brought the kind of experience I find myself longing for now.
Dirt bikes. Bowhunting in the backcountry. Getting completely lost in the woods of Appalachia. Even those long stretches of isolation in war zones… they all made me feel alive.
These days, most of my time is spent helping others architect systems of work, planning for uncertain futures, and chasing the ever-elusive EBITDA target. And while I love what I do, that craving for raw, unfiltered experience is louder than ever.
And as soon as Ford is old enough, I want to teach him all of it. How to disconnect. How to find himself in the wild. How to be brave, capable, and curious. Because someday, he’ll face a world in transition too, and I want him to know how to meet it head-on.
What do you say, Josh and Pat—let’s plan a trip.
A Small Business To Know: GoldLeaf Interior
My friend Kelly is a badass.
Not just because she’s endlessly supportive of literally everything Jenelle and I do;
Not just because she’s a community leader through her work with March of Dimes;
Not just because she runs a business with heart and style.
She’s all of that—and on top of it, she and her husband Teal are a ton of fun.
Kelly is the visionary behind GoldLeaf Interior. While she’s brilliant at capturing whatever style best fits her clients, I’d describe her natural aesthetic as NYC edge meets Southern charm.
It’s refined.
It’s bold.
It’s unapologetically cool.
If you’re looking to elevate your space, or just want a little inspiration, check out GoldLeaf.
I make no apologies for bragging on my friends.
An Update from the Homefront
I love being a dad. The whole experience over the past 12 weeks has changed everything. I’m more focused than ever on being a leader in my home and steering our family toward the goals we share.
I’m still figuring out how to be a dad. I feel a deep responsibility to raise Ford to be a strong, compassionate man—someone who leads, protects, and lifts up others.
At the same time, I want to shield him from unnecessary hardship while making sure he has the skill and fortitude to take on any challenge headfirst, with confidence—and, when needed, with violence of action.
If you’ve figured out how to strike that balance, I’m all ears.
As always, Thank You.
It’s been a whirlwind of a month. Between planning, board meetings, international travel, and everything happening at home, life’s been full—and fast.
Through it all, I keep coming back to the same theme: clarity, focus, and staying anchored to what really matters. That’s what this season is about for me.
While I’m thinking of it, huge congrats to Micah and Carly on your engagement this week! Carly, we’re so excited to officially welcome you to the family.
And to you, thank you for reading. Month after month, I’m grateful you take the time to follow along as I share thoughts, lessons, and a little behind-the-scenes. This newsletter is mostly a creative outlet for me, and I hope it brings you some value—and maybe a little entertainment too.
Until next time,
AM
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